This article discusses the question: where to with sustainable urbanism? It includes a historic review of the concept of sustainable urbanism and reviews of recent literature in the field of eco-cities. Through these reviews, it deliberately interrogates new pathways for sustainable urbanism. The result of this investigation is the insight that there are six design principles that are required to create a sustainable city: a design in which cycles are closed, redundancy is built in, anti-fragility is created, citizens are seen as (design) experts, the landscape is used as the basis, and innovative, rule-breaking designs are developed. These six design principles are then captured in three comprehensive concepts, which together support the design of a sustainable city: the design approach needs to be a (1) society-based; (2) complexity-led, and (3) landscape-driven design approach.